Potassium Carbonate → HCID 178468147, compound

HRID 1779624Notes

Reaction equation

HRID 1779624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])C=C[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16]>CC(C)=O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][SH:8]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7]1)[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162573-ChlorothiophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 178468147HCID 178468147, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
23 °C

Procedure

A three-neck round bottom flask was charged with 3-chloro-thiophenol (20.0 g, 0.138 mol) and potassium carbonate (21 g, 0.15 mol) in acetone (220 ml) and treated with a dropwise addition of bromoacetaldehyde diethyl acetal. After stirring for 17 hours at 23° C., the slurry was filtered through a small plug of celite, the filtrate evaporated under reduced pressure and the residue diluted with diethyl ether and water. The organics were washed with brine, dried over sodium sulfate, and evaporated to a rust-colored oil weighing 35.1 g (97%). FDMS m/e=260 (M+).

Workup

  1. filtrationthe slurry was filtered through a small plug of celite
  2. customthe filtrate evaporated under reduced pressure
  3. additionthe residue diluted with diethyl ether and water
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a rust-colored oil

Sources & evidence

ORD record
ord-5068c6beda8941ea9b531f682ea194c4
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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